USPTO Patents Application 09750990

o3' iG'OOj

PATENT
674509-2028

IN THE UNITED STATES PATENT AND TRADEMARK OFFICE

pplicant(s)
U.S. Appln. No.
U.S. Filing Date
Title of Invention
Examiner
Art Unit

Confirmation No.

Jom Borch Soe

09/750,990

December 28, 2000

Foodstuff

Leslie A. Wong

1794

9458

745 Fifth Avenue, New York, NY 10151

EXPRESS MAIL

Mailing Label Number: EM 132046046 US

Date of Deposit:

March 13.2009

I hereby certify that this paper or fee is being deposited with the
United States Postal Service "Express Mail Post Office to
Addressee" Service under 37 CFR 1.10 on the date indicated above
and is addressed to: Commissioner for Patents, P.O. Box 1450,
Alexandria, VA 22313-1450,

JTyr

Typed or printed name of person mailing paper o r fee )^

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COMMUNICATION FORWARDING PRIORITY DOCUMENTS

Commissioner for Patents

P.O. Box 1450

Alexandria, VA 22313-1450

Dear Sir:

Enclosed are certified copies of the priority documents for the above-identified
appHcation. Applicant hereby claims priority under 35 U.S. C. §§ 119 and/or 120 from
Application No. GB 9824758.8 filed November 11, 1998 and Application No. GB 9815905.6
filed July 21, 1998.

Acknowledgment of the claim of priority and receipt of the certified copies are requested.

Respectfully submitted,
FROMMER LAWRENCI

Thomas J. KowalsK, Reg.'^^o. 32,147
Tel. No. (212) 588-0800

WORLD INTELLECTUAL PROPERTY
ORGANIZATION

ORGANISATION MONDIALE
DE LA PROPRIETE INTELLECTUELLE

i^aaj uuji

organizaci6n mundial
de la propiedad evtelectual

BCEMHPHAfl OPrAHHSAmifl
HHTEJIJIEKXyAJIbHOft COBCTBEHHOCTH

CERTIFICATION

It is hereby certified that the attached copy is a true copy of the certified copy of
British patent application no. GB 9815905.6 filed on 21 July 1998 (21.07.1998),
which certified copy was established by the British Patent Office and transmitted
to the International Bureau under PCT Rule 17.1 .

By: The International Bureau

34, chemin des Colombettes, 121 1 Geneve 20, Suisse - Tel. +41 22 338 91 1 1 - Fac-simile +41 22 733 54 28
Internet: http://www.wipo.int - http://www.ompi.int - e-mail: wipo.mail@wipo.int
Banque: Credit Suisse, Geneve, compte OMPl - IBAN No. CHS I 0483 5048 7080 8100 0 - SWIFT/BIC: CRESCHZZ80A
Post Finance, Geneve, OMPI No. 12-5000-8 - IBAN No. CH03 0900 0000 1200 5000 8 - SWIFT/BIC: POFICHBE

Date: 23 January, 2009

Pkteot
Office

PRIORITY
DOCUMENT

^

PCT / IB 9 3 5 i

I I 1 0. 11. 99

INVESTOR IN PEOPLE

The Patent Office
Concept House
Cardiff Road
Newport
Sou th WqIoo

2 NOV 1999

IWIPO

PCT

I, the undersigned, being an officer duly authorised in accordance with Section 74(1) and (4)
of the Deregulation & Contracting Out Act 1994, to sign and issue certificates on behalf of the
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originally filed in connection with the patent application identified therein.

In accordance with the Patents (Companies Re-registration) Rules 1982, if a company named
in this certificate and any accompanying documents has re-registered under the Companies Act
1980 with the same name as that with which it was registered immediately before re-
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pic, P.L.C, or PLC.

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ibjects the company to certain additional company law rules.

9 ,4 .

Signed

Dated 1 November 1999

An Bxcculi ve Agency of the Deparlmenl oTTrade and Industry

ts Forr ./77

^aients Act 1977
^Rule 16)

Office

i CO

Request for a grant of a patent

(See the notes on the back of this form. You can also get
an explanatory leaflet from the Patent Office to help
you fill in this form)

9815905.6

2l JULi^^SB.

The Patent Office

Cardiff Road
Nevvpon
Gweni NP9 IRH

Your reference

P/5074.GB

Patent application number

(The Patent Office will fill in this part)

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(underline all surnames)

Patents ADP number (if you know it)

If the applicant is a corporate body, give the country/state of its
incorporation

Danisco A/S
Langebrogade 1
PO Box 17

DK-1001 Copenhagen K
Denmark

Denmark

Title of the invention

Foodstuff

Name of your agent (if you hove one)

"Address for service" in the United Kingdom to which all
correspondence should be sent
(including the postcode)

Patents ADP number (if you hove one)

D YOUNG & CO

21 NEW FETTER LANE

LONDON

EC4A IDA

59006 - '

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Description

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Abstract

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Signature Date

21 07 98

D YOI/nG & €0
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12. Name and da}rtiine telephone number of the person to contact in David AlCOCk
the United Kingdom

01703 634816

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prohibited or restricted under Section 22 of the Patents Act 2977. You will be informed if it is necessary to prohibit or restrict your invention in this way Furthermore
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Foodstuff

The present invention relates to a foodstuff. More particularly, the present invention
relates to a foodstuff comprising at least one functional ingredient which has been
5 generated in situ by a conversion agent.

Traditionally food was prepared in the private households and the constituents of the
food or of the foodstuff were brought to the kitchen of the household where the food or
foodstuff was prepared shortly before consumption.

10

Industrial development increased the demand for the reduction of the time and effort
required to prepare food or foodstuffs. Thus there has been a massive expansion in the
industrial preparation of food.

15 Recently, there has been increased demand for improvements in the quality of
industrially prepared food. In particular there is demand for improved taste, eating
quality and shelf life. In an attempt to address these demands for improved foodstuffs,
industrial food producers have utilised and have relied upon functional ingredients to
meet the demands for quality and shelf life. Functional ingredients such as emulsifiers,

20 hydrocolloids, preservatives, antioxidants, colourings and flavourings are widely used in
the food industiy.

More recently, there has been demand from consumers to reduce the number of
additives, such as functional ingredients, included in foodstuffs. Thus, there is a desire
25 to prepare industrially foodstuffs meeting the quality requirements of consumers whilst
minimising the number of additives in the final foodstuffs.

Both Douglas B. Samey et ai. Enzymatic Synthesis of Sorbitan Esters Using a Low-
Boiling-Point Azeotrope as Reaction Solvent, Biotechnology and Bioengineering, 1997
30 vol. 54(4) and J. A. Arcosm et ai. Quantitative Enzymatic 'Production of 6.0-
Acylglucose Esters, Bioteclinology and Bioengineering 1998 57(5), teach the use lipase
for the production of emulsifiers. The teachings require the synthesis of emulsifiers in

9

an organic solvent system. The emulsifier is then isolated from the organic solvent
system before use in food.

A. Coteron et al.. Reactions of Olive Oil and Glycerol over Immobilised Lipases,
5 JAOCS, Vol. 75, no. 5 (1998) reports the use of immobilised Upase in the reaction of
olive oil. and glycerol. Subsequent to the reaction the immobilised lipase is removed
from the reaction mixture.

JP-A-901 88214 reports the use of an immobihsed lipase for the hydrolysis and ester
10 exchange of triglyceride. In this process part of the triglyceride is partially hydrolysed
to free fatty acid. The partially hydrolysed triglyceride product is used for production of
margarine.

JP-A-5211852 discloses the addition of a lipase to a mixture of fat and water. The
15 product prepared in this method may be used in the production of mayonnaise. The
mayonnaise is prepared at a temperature such that the activity of lipase is not reduced.

The present invention addresses the problem of the prior art

20 According to a first aspect of the present invention there is provided use of a conversion
agent to prepare from a food material a foodstuff comprising at least one functional
ingredient, wherein the at least one functional ingredient has been generated from at
least one constituent of the food material by the conversion agent.

25 According to a second aspect of the present invention there is provided a process for
preparing a foodstuff comprising the steps of (i) providing a food material; (ii)
contacting the food material with a conversion agent such that a functional ingredient is
generated by the conversion agent from at least one constituent of the food material.

30 According to a third aspect of the present invention there is provided a foodstuff
prepared from a food material, wherein the foodstuff comprises at least one functional
ingredient, and wherein the at least one functional ingredient has been generated from at

3

least one constituent of the food material by a conversion agent.

By the term ''functional ingredient" we mean a constituent of the foodstuff which
performs a specific function in the foodstuff Preferably by the term "ftinctional
5 ingredient" we mean an emulsifier, hydrocoUoid, preservative, antioxidant, colouring,
flavouring, and/or viscosity modifier.

By the term "foodstuff we mean a substance which is suitable for human or animal
consumption.

10

The above aspects of the present invention are advantageous as they overcome the
problems associated with the prior art.

The present invention utiUses a , conversion agent, such as enzyme, during the
15 production of a foodstuff to generate one or more functional ingredients, for example
emulsifiers, antioxidants or preservatives, from a constituent of a food material (i.e.
ingredients) from which the foodstuff is prepared. The constituent(s) may be a fat, for
example. Thus, instead of adding food additives produced by traditional chemical
synthesis, the present invention provides for the in situ synthesis of a required frmctional
20 ingredient.

Traditional chemical synthesis of functional ingredients is problematic because
syntheses are often carried out under extreme conditions, such as high temperatures (e.g.
-200°C). Under extreme conditions, side reactions may occur. Thus, although the
25 resultant product may be substantially pure, it may contain undesirable components. To
eliminate undesirable components, reactions must be closely controlled and/or the
resultant product may require purification, adding to a production process. The present
invention aims to overcome these disadvantages.

30 Moreover, by generating the functional ingredient from at least one constituent of the
food material using a conversion agent, the foodstuff comprises at least one less
^'additive" material. This is advantageous because of the improvement in the ease of

4

- production. Moreover, the foodstuff may contain less "additives". The reduction or
eUmination of "additives" is desirable to consumers and inclusion of additives often
must be declared to the consumer in the ingredients listing on the foodstuff Thus, the
present invention is further advantageous.

5

The food material may be contacted with the conversion agent in any manner. The food
material may be contacted with the conversion agent in an immobilised form. The food
material may simply be added to the conversion agent or vice versa. In the latter aspect,
the conversion agent may be subsequently removed from the food material/foodstuff or
10 may remain in the food material/ foodstuff. In a preferred aspect the conversion agent is
present in the foodstuff

The above preferred aspect is advantageous because one may contact the food material
with the conversion agent to thereby provide a foodstuff suitable for consumption. No

15 further processing or addition of ingredients may be required; a foodstuff comprising a
required functional ingredient is produced. Thus a foodstuff may be provided in which
a required functional ingredient has been simply generated. Synthesis of the functional
ingredient discretely from the foodstuff followed by subsequent addition is not required.
Moreover, provided of course the conversion agent is suitably chosen so that it is

20 compatible with a foodstuff i.e. it is edible, frirther processing of the foodstuff may not
be necessary. However, the present invention encompasses foodstuffs which have been
further processed.

Preferably, the conversion agent is a catalyst.

25

In a preferred aspect, the conversion agent is an enzyme. This aspect is particularly
preferred because enzymes are readily available, may be chosen to convert a specific
constituent of the food material and/or may be chosen to generate a specific functional
ingredient. Yet further, enzymes may be denatured by heat. Thus in a further preferred
30 aspect, the foodstuff/food material is heated after generation of the functional
ingredient. The enzyme will be denatured and may then constitute protein. This is
advantageous because the denatured enzyme need not be declared on the foodstuff/food

material ingredients.

The use of enzymes is advantageous because denatured enzymes are considered,
particularly under food labelling regulations, to constitute a processing aid. Inactivated
enzymes are not considered to be additives; the addition of additives to foodstuffs is
undesirable to riiany consumers.

Inactivation of the conversion agent, in particular denaturation of the enzyme, is
advantageous because it allows one to control the amount of functional ingredient
aenerated. For example, the generation of the functional ingredient may be monitored

(for example by measurement of the functional properties of the food material) or the
rate thereof determined. One may then terminate the generation of the functional
in^^redient when a suitable amount of functional ingredient has been generated, by
heating the food material. Thus., the amount of the functional ingredient and the
properties of the food material/foodstuff may easily be controlled.

Preferably, the enzyme is selected from lipases (EC 3.1.1.3), esterases, amylases,
xylanases, proteases, derivatives and mixtures thereof More preferably, the enzyme is
selected from hpases, esterases, derivatives and mixtures thereof.

Preferably the enzyme is an enzyme as described in and/or as claimed in Danish Patent
Application No. 0400/97. In other words preferably the enzyme is a polypeptide in
glycosylated or non-glycosylated form capable of exhibiting lipase activity wherein the
polypeptide comprises at least one amino acid sequence selected from the group
consisting of

(I) Ser-Val-Ser-Thr-Ser-Thr-Leu-Asp-Glu-Leu-Gln-Leu-Phe-Ala-Gln-Trp-Ser-Ala-
Ala-Ala-Tyr-Xaa-Ser-Asn-Asn

(II) Val-His-Thr-Gly-Phe-Trp-Lys

(III) Ala-Trp-Glu-Ser-Ala-Ala-Asp-Glu-Leu-Thr-Ser-Lys-Ile-Lys

6

where Xaa represents an amino acid selected from the group consisting of Ala, Arg,
Asn, Asp, Cys, Gin, Glu, Gly, His, He, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr and
VaL

5

Preferably, the enzyme is isolated from a plant (preferably soy bean, rice bran and/or
sunflower seed), an animal (preferably an animal pancreas) or a microorganism.
Preferably, the microorganism selected from Aspergillus niger, Rhizopus delemar,
Rhizopiis arrhizus, Miicor miehei, Pseiidomonas sp., Candida nigosa, Pencilium
10 roqueforti, Pencilium cyclopium, Aspergillus tubingensis, Candida cylindracea,
Thermomyces lanuginosus, Mucor Javanicus, Candida ajitarctica, Chromobacterium
viscosum, Pseudomanas fluorescens, mutants and combinations thereof.

Preferably, the conversion agent is present in the foodstuff. More preferably, the
'15 conversion agent is present in an inactive form or in a denatured form in the foodstuff.

Preferably, the functional ingredient is generated from at least two constituents of the
food material. In this aspect at least two constituents of the foodstuff may interact
and/or react and/or combine together to generate at least one functional ingredient.
20 Preferably, the functional ingredient is generated from a first constituent and a second
constituent of the food material.

Preferably, the first constituent and the second constituent are constituents of the
foodstuff In this aspect, the functional ingredient is generated from a first constituent
25 and a second constituent of the food material and the first constituent and second
constituent are also present in the foodstuff Thus the functional ingredient may be
generated from constituents/ingredients of the food material which are only partially
used to generate the functional ingredient. The remainder of the
constituents/ingredients may be present in the foodstuff.

30

In a preferred aspect of the present invention the first constituent of the food
material/foodstuff is hydrophobic and/or lipophilic.

7

Preferably, the first constituent of the food material/foodstuff is selected from esters,
monoglycerides, diglycerides, triglycerides, fats, including lard, tallow and butter fat;
fatty acids, fatty acid esters, waxes, wax esters, oils including oils extracted from or
5 derived from palm oil, sunflower oil, soya bean oil, safflower oil, cotton seed oil,
ground nut oil, com oil, olive oil, peanut oil, coconut oil and rape seed oil; derivatives
and mixtures thereof. More preferably, the first constituent of the food
material/foodstuff comprises or is an ester or a triglyceride.

10 The term "triglyceride" preferably means a triester of an alcohol, preferably glycerol,
- and a fatty acid. More preferably the triglyceride fatty acid is a triester of an alcohol,
preferably glycerol, and a C4 to C24 fatty acid. Preferably the triglyceride fatty acid has
an iodine value of from 0 to 60.

15 Preferably, the triglyceride is selected from triglycerides having a fatty acid chain length
of no greater than 14 carbons, triglycerides having a fatty acid chain length of from 4 to 14
carbons, triglycerides having a fatty acid chain length of from 6 to 14 carbons,
triglycerides having a fatty acid chain length of from 8 to 14 carbons, triglycerides having
a fatty acid chain length of from 10 to 14 carbons, triglycerides having a fatty acid chain

20 length of 12 carbons, triglycerides having a fatty acid chain length of from 16 to 24
carbons, triglycerides having a fatty acid chain length of from 16 to 22 carbons,
triglycerides having a fatty acid chain length of from 18 to 22 carbons, triglycerides
having a fatty acid chain length of from 18 to 20 carbons, mixtures and derivatives thereof.

25 In a preferred aspect of the present invention the second constituent of the food
material/foodstuff is hydrophilic.

Preferably, the second constituent of the food material/foodstuff is selected from a
constituent comprising a hydroxy group (-0H), polyvalent alcohols, including glycerol;
30 water, ethanol, sugars including sucrose, fructose,' glucose (dextrose), lactose, and
galactose; dextrin, sorbitol, mannitoL fruit acids and hydroxy acids including citnc acid,
tartaric acid, lactic acid and ascorbic acid; mixtures and denvatives thereof More

8

preferably, the second constituent of the food material/foodstuff is glycerol.

In a further preferred embodiment, the first constituent of the food material/ foodstuff is
an ester, preferably a triglyceride and the second constituent of the food
5 material/foodstuff is a constituent comprising a hydroxy group (-OH), Preferably, the
first constituent of the food material/foodstuff is a triglyceride. Preferably, the second
constituent of the food material/foodstuff is an alcohol, more preferably a polyvalent
alcohol, yet more preferably glycerol.

10 In a highly preferred embodiment, the first constituent of the food material/foodstuff is a
constituent comprising at least two ester groups, preferably a triester, more preferably a
triglyceride and the second constituent of the food material/foodstuff is a sugar or a
sugar alcohol. In this highly preferred aspect the first constituent and the second
constituent may interact on contact with the a conversion agent to generate an ester

15 derived from the first constituent wherein the ester has a lower degree of esterification
than the first constituent, and a sugar ester. This is extremely advantageous because the
ester may act as a functional ingredient, such as an emulsifier, and the sugar ester may
also act as a functional ingredient, such as an emulsifier or an anti-oxidant. Thus, two
functional ingredients may be generated from two constituents by a conversion agent.

20

In the above highly preferred aspect the second constituent is preferably ascorbic acid.
Ascorbic acid ester is an antioxidant.

Thus, in a further broad aspect of the present invention there is provided a foodstuff
25 prepared from a food material, wherein the foodstuff comprises at least two functional
ingredients, and wherein the at least two functional ingredient have been generated from
a first constiment of the food material and a second constituent of the food material by a
conversion agent. Preferably, the first constituent is a constituent comprising at least
two ester groups, preferably a triester, more preferably a triglyceride. Preferably, the
30 second constituent is a sugar or a sugar alcohol, more preferably ascorbic acid.

The conversion agent may be contacted with the all of the food material or a portion

9

thereof. In the latter case, a portion of the food material may be removed from the total
amount of food material. After contacting the conversion agent with the portion of food
material, the portion may be returned to the remainder of food material. The portion of
the food material may comprises from 0.1 to 10 wt % of the total food material,
5 preferably from 0.1 to 5 wt % of the total food material, preferably from 0.1 to 2 wt %
of the total food material, more preferably from 0.5 to 1 wt % of the total food material.

The conversion agent may be contacted with a carrier prior to contact with the food
material. Preferably, the carrier is a constituent of the food material. Preferably, the
10 carrier is a first constituent or a second constituent of the food material as defined
above. More preferably, the carrier is glycerol.

Preferably, the functional ingredient of the present invention is generated by a reaction
selected from alcoholysis, preferably glycerolysis, hydrolysis, interesterification, and
15 combinations thereof More preferably the functional ingredient is generated by a
alcoholysis reaction, preferably a glycerolysis reaction.

Preferably, the functional ingredient comprises less than 5 wt % of the foodstuff
Preferably, the functional ingredient comprises from 0.01 to 4 wt % of the foodstuff
20 Preferably, the functional ingredient comprises from 0.01 to 2 wt % of the foodstuff
Preferably, the functional ingredient comprises from 0.01 to 1 wt % of the foodstuff
Preferably, the functional ingredient comprises from 0.01 to 0.5 wt % of the foodstuff
Preferably, the functional ingredient comprises from 0.01 to 0.3 wt % of the foodstuff

25 Preferably, the functional ingredient is selected from emulsifiers, hydrocoUoids,
preservatives, antioxidants, colourings and flavourings. More preferably, the functional
ingredient is an emulsifier. In this aspect, preferably the emulsifier comprises from 0. 1
to 0.3 wt % of the foodstuff

30 The emulsifier may comprises or may be selected from monoglycerides, diglycerides,
derivatives and mixtures thereof

10

A person skilled in the art will appreciate that the at least one constituent of the food
material from which the functional ingredient is generated may be selected to provides a
required functional ingredient. Thus in the above aspect wherein the functional
ingredient is an emulsifier, preferably an emulsifier selected from monoglycerides,
5 diglycerides, derivatives and mixtures thereof, the at least one constituent may be, for
example, a triglyceride and a polyvalent alcohol.

In a preferred- aspect the present invention provides foodstuff as defined above wherein
the foodstuff is selected from baked goods, including breads, cakes, sweet dough

10 products, laminated doughs, liquid batters, muffins, doughnuts, biscuits, crackers and
cookies; confectioner>% including chocolate, candies, caramels, halawa, gums, including
sugar free and sugar sweetened gums, bubble gum, soft bubble gum, chewing gum and
puddings; frozen products including sorbets, preferably frozen dairy products, including
ice cream and ice milk; dairy products, including coffee cream, whipped cream, custard

15 cream, milk drinks; mousses, whipped vegetable creams, meat products, including
processed meat products; edible oils and fats, aerated and non-aerated whipped
products, oil-in- v/ater emulsions, water-in-oil emulsions, margarine, shortening and
spreads including low fat and very low fat spreads; dressings, mayonnaise, dips, cream
based sauces, cream based soups, beverages, spice emulsions, sauces and mayonnaise.

20

In one aspect of the present invention the foodstuff is a foodstuff other than mayonnaise.

The claims of the present application are to be construed to include each of the
foodstuffs Usted above.

25

In a preferred embodiment the foodstuff of the present invention is a spread, preferably
a margarine.

Thus in a preferred aspect the present invention provides a margarine prepared from a
30 food material, wherein the foodstuff comprises at least one ftinctional ingredient, and
wherein the at least one functional ingredient has been generated from at least one
constituent of the food material by a conversion agent.

i

1 1

In a further preferred embodiment the foodstuff comprises greater than 30 wt % fat (i.e.
triglycerides), more preferably greater than 40 wt % fat, yet more preferably greater than
50 wt % fat.

5

The foodstuff may comprise an emulsion of oil and water. The emulsion may be an oil-
in-water emulsion. The emulsion may be an water-in-oil emulsion.

The invention will now be described, by way of example only, with reference to the
10 following examples

EXAMPLES

Example 1 - Full-fat Table Margarine

15

Full-fat table margarine is used for spreading on bread and household baking.

Each of fat blends A, B and C Usted in Table 1 were treated with lipase as follows. 1 part
of the fat blend is heated to 50°C during stirring 0.2 part of hpase (obtained from
20 Aspergillus tubingensis) dispersed in glycerol is added. The fat blend is reacted for 12
hours at 50 ^^C and then shortly heated to 100 °C to denature the enzyme.

Table 1

Fat blends

A

B

C

Margarine used at approx.

5-10°C

20-25°C

■ 25-30°C

Soya41°C

20

Soya 35°C

20

Soya oil

60

25

20

12

Palm 43°C

-

25

30

Palm oil

-

50

50

SFC* values of fat blends (TUPAC method)

A

B

C

5°C

34

47

54

10°C

28

45

50

20°C

14

26

30

30°C

3

10

12

35=C

0

5

7

40°C

0

1

2

Slip melting point °C (AOCS 3-25 method)

26.3

36.9

36.8

* Solid fat content

The treated fat blends were then processed in accordance with the following steps to
5 prepare a recipe shown in Table 2

1. Blend the water phase ingredients. (If required, pasteurise the water phase by
heating to approx. 80°C). Adjust pH with Ferment Flavouring 4646.

2. Melt the fat phase, and temper to approx. 40-45°C. Add the p-carotene.
10 3. Add the flavouring.

4. Add the water phase to the fat phase, stirring continuously.

5. Cool in a tube chiller (normal capacity, normal cooling) to an outlet temp of S-IC'C.

13

Table 2

Water phase:

Water

16.0%

Skimmed milk powder or whey powder

1.0%

Salt

1.0%

pH 5.0-5.5 with Ferment Flavouring 4646*

Fat phase:

Lipase treated fat

1.2%

Soya lecithin

0.2%

P-carotene

4 ppm

Fat blend

80.6%

Butter Flavouring 3559**

0.01%

* Ferment Flavouring 4646 - a nature-identical, water-soluble flavouring which ensures a
5 good, lactic and fermented taste. Used for direct acidification of the v/ater phase to ensure
the taste similar to that obtained by microbial femientation of the milk
** Butter Flavouring 3559 - a nature-identical, fat-soluble flavouring which provides a
rich, fermented butter taste.

10 The fat contacted with lipase generated an emulsifier, a functional ingredient which is
important in the preparation of margarine. Each of the margarines prepared from fat
blends A, B and C was visually inspected and found to substantially identical in
appearance to conventionally prepared margarine. No separation of the oil and water
phases was observed. Each of the margarines prepared from fat blends A, B and C was

15 also spread on bread and tasted. The organoleptic properties of each margarine was
pleasant and were felt by the taster to be substantially identical to those of conventionally
prepared margarine.

Fxample 2 - 60% Fat Spread with Protein

20

60% fat spread with protein is used for spreading on bread and open pan frying instead of
full-fat products.

14

Each of fat blends A and B listed in Table 3 were treated with lipase as follows. I part of
the fat blend is heated to 50°C during stirring 0.2 part of lipase (obtained from Rhizopiis
arrhizus) dispersed in glycerol is added. The fat blend is reacted for 12 hours at 50 °C
5 and then shortly heated to 100 °C to denature the enzyme.

Table 3

Fat blends

A

B 1

Spread used at approx.

5-10°C

20-25°C 1

Soya41°C

25

20

Soya 35°C

-

45

Soya oil

75

35

SFC values of fat blends (lUPAC method)

A

B

5°C

23

48

10°C

19

46

20°C

9

28

30°C

2

8

35°C

0

2

40°C

0

0

Slip melting point °C (AOCS 3-25 method)

26.6

31.7

The treated fat blends were then processed in accordance with the following steps to
10 prepare a recipe shown in Table 4

1. Blend the water phase ingredients. (If required, pasteurise the water phase by
heating to approx. SC'C). Adjust pH.

2. Melt the fat phase, and temper to approx. 40-45°C. Add the P-carotene.

3. Add the flavouring.

15

4. Add the water phase to the fat phase, stirring vigorously.

5. Crystallise and knead vigorously in a tube chiller (80% of normal capacity, NH3 -
15°C, 2 tubes) to an outlet temperature of S-IO'^C

Table 4

Water phase at pH 5.5:

Water

37.9%

Whey powder

1.0%

Salt

1.0%

K-sorbate

0.1%

Fat phase:

Lipase treated fat

1 .4%

P-carotene

4 ppm

Fat blend

58.6%

Butter Flavouring 3559

0.01%)

The fat contacted with lipase generated an emulsifier. Both of the margarines prepared
from fat blends A and B was visually inspected and found to substantially identical in
10 appearance to conventionally prepared margarine. No separation of the oil and water
phases was observed. Both of the margarines prepared from fat blends A and B was also
spread on bread and tasted. The organoleptic properties of each margarine was pleasant
and were felt by the taster to be substantially identical to those of conventionally prepared
margarine.

15

Example 3 - 40% Fat S pread with Whev Powder

Fat blend A listed in Table 3 above was treated with lipase as follows. 1 part of the fat
blend is heated to 50°C during stirring 0.2 part of lipase (obtained from Candida nigosa)
20 dispersed in glycerol is added. The fat blend is reacted for 12 hours at 50 °C and then
shortly heated to 100 °C to denature the enzyme and used for 40%) fat spread production.
The spread had a composition shown in Table 5 below.

16

Table 5

Water phase at pH 5.5

Water

55.16%

Salt

1.2%

K-sorbate

0.1%

Whey powder

1.0%

GRINDSTED"^^^^ Pectin
LFS 100

1.0%

Fat phase

Fat blend

- 25 parts soya 41°

- 75 parts liquid oil

39.5%

P-carotene

4ppm

Butter Flavouring 2873

0.01%

Butter Flavouring 3507

0.01%

Lipase treated fat

2.0%

The fat contacted w^ith lipase generated an emulsifier. The low-fat spread was stable and
5 had good water dispersion. Sensory evaluation of the sample showed that they had a very
good flavour release and colour.

Example 4 - Filling Cream.

10 Each of fat blends A and B listed in Table 3 above were treated with lipase as follows. 1
part of the fat blend is heated to 45°C during stirring 0.2 part of lipase (obtained from
Rhizopus delemar) dispersed in glycerol is added. The fat blend is reacted for 12 hours at
45 °C and then shortly heated to 100 °C to denature the enzyme and used for filling cream
production..

15

Filling cream was made in a ice cream freezer with mono-pump (capacity 27 kg/hr).
Nitrogen blown in after the pump and before the cooling cylinder. Outlet temperature:
15-17^C.

17

The filling cream spread had a composition shown in Table 6 below.

Table 6

Water phase

Water

12.5%

GRE^roSTED™ Pectin LFS 100

0.5%

SMP

8.0%

Sucrose

9.9%

-

Invert sugar

9.0%

Sorbitol 70%

8.0%

Glucose syrup

14.0%

Glycerol

7.0%

K-sorbate

0.1%

Fat phase

Lipase treated fat

3,0%

Lecithin

0,4%

Fat blend (100% coconut 31 "C)

27.6%

Butter flavouring 2598

0.03%

The fat contacted with lipase generated an emulsifier. The filling cream was smooth with
good flavour release. Specific gravity of the cream: 0.8 g/ml.

Example 5 - Ice cream

1 part of soya fat 41 ° is heated to 45 °C during stirring 0,2 part of lipase (obtained from
Aspergillus niger) dispersed in glycerol is added. The fat blend is reacted for 12 hours at
45 °C and then shortly heated to 100 °C to denature the enzyme and used for ice cream
production.

The treated fat was then processed in accordance with the following steps to prepare a
recipes shown in Table 7

1 . Heat all liquid ingredients to approx. 40 °C

18

2. Add dry ingredients, (stabiliser blend is mixed with sugar before addition)

3. If butter/butter oil or veg. fat is used it must be melted separately and added to the mix
at 40 °C, or via a static mixer at the entrance to the homogeniser by means of a dosing
pump.

5 4. Pasteurise at 80 -85 ^C/20-40 seconds

5. Homogenise at 80 °C (190 bar for recipe 1 and 175 bar for recipe 2)

6. Cool to ageing temperature , 4

7. Freeze in continuos freezer to desired overrun (100% recommended)

8. Harden in tunnel at -40 °C
10 9- Store below -25 °C

Table 7

Recipe

1

Milk fat

2

Veg. fat

Dairy cream, 38%

23.65

Skimmed milk

53.30

Skimmed milk powder

4.90

11.30

Vegetable fat (HCO)

8.00

Sugar

12.00

12.00

Glucose syrup, DE 42, 75% TS

5.25

5.25

Stabiliser blend

0.2

0.2

Lipase treated fat

0.6

0.6

Grindsted Flavouring 2976

0.1

0.1

Colour

+

+

Water

62.55

19

The fat contacted with Hpase generated an emulsifier. Ice cream of both recipes
crood taste and excellent creamy mouthfeel.

5 F.xample 6 -Margarine

10

15

In a vessel 0.6 part of sun flower oil and 0.4 part of palm oil and 0.15 part of lipase from
Rhizopus arrhizus dissolved glycerol/water is added. The reaction is continued for 20
hours at 45°C and then shortly treated by lOQOC in order to inactivate the enzyme.

Two recipes were prepared. These recipes are shown in Table S below. Recipe 1 was in
accordance with a prior art method - a previously prepared mono/di glyceride emulsifier
(DIMODAN® CP-available from Danisco Ingredients, Denmark) was added. Recipe 2
was in accordance with the present invention. In recipe 2, 1.7% of the fat phase was
provided by the above lipase treated fat. The lipase treated fat was added to the fat
blend for margarine production and the margarine is produced by standard procedures
for margarine production.

Table 8

20

Recipe

1

2

WATER PHASE

Water

480

480

Salt

30

30

Skim Milk Powder

30

30

Potassium Sorbate

3

EDTA

0.45

0.45

pH

5.5

5.5

FAT PHASE

Soya 41"

490

481

Soya j:)

490

481

20

Soya oil

1471

1444

DIMODAN"^ CP

6.0

-

Lipase

51.0

PPM P-carotene

0.5

0.5

Flavourings

0.6

0.6

The fat contacted with Upase generated an emulsifier. The margarine in accordance with
the present invention was visually inspected and found to substantially identical in
appearance to the conventionally prepared margarine. No separation of the oil and water
5 phases was observed. The margarine in accordance with the present invention was also
spread on bread and tasted. The organoleptic properties of the margarine was pleasant and
were felt by the taster to be substantially identical to those of the conventionally prepared
margarine.

10 Example 7 -Margarine

In a vessel 1 part of palm oil and 0.15 part of esterase from Candida dissolved in sugar
(sucrose)/water is added. The reaction is continued for 20 hours at 55°C and then shortly
treated by lOO^C in order to inactivate the enzyme.

15

1% of this reaction mixture is added to a fat blend for margarine production and the
margarine is produced by standard procedures for margarine production.

The reaction mixture gives good water in oil emulsification properties.

20

Example 8 -Margarine

In a vessel 1 part of palm oil and 0T5 part of lipase from Candida dissolved citric
acid/glycerol/water is added. The reaction is continued for 20 hours at 55°C and then
25 shortly treated by lOO^C in order to inactivate the enzyme.

21

1% of this reaction mixture is added to a fat blend for margarine production and -the
margarine is produced by standard procedures for margarine production.

The reaction mixture gives good water in oil emulsification and also contributes to
5 reduce spattering when the margarine is used for frying.

Example 9 -Margarine

In a vessel 1 part of palm oil and 0.05 part of lipase from Aspergillus niger dissolved
10 water is added. The reaction is continued for 20 hours at 40°C and then shortly treated
by lOO^C in order to inactivate the enzyme.

1% of this reaction mixture is added to a fat blend for margarine production and the
margarine is produced by standard procedures for margarine production.

15

The reaction mixture gives good water in oil emulsification.

All publications mentioned in the above specification are herein incorporated by
20 reference. Various modifications and variations of the described methods and system of
the invention will be apparent to those skilled in the art without departing from the
scope and spirit of the invention. Although the invention has been described in
connection with specific preferred embodiments, it should be understood that the
invention as claimed should not be unduly limited to such specific embodiments.
25 Indeed, various modifications of the described modes for carrying out the invention
which are obvious to those skilled in chemistry or related fields are intended to be
within the scope of the following claims.

22

CLAIMS

1. Use of a conversion agent to prepare from a food material a foodstuff comprising at
least one functional ingredient, wherein the at least one functional ingredient has been
5 generated from at least one constituent of the food material by the conversion agent.

.2. A process for preparing a foodstuff comprising the steps of

(i) providing a food material;

(ii) contacting the food material with a conversion agent such that a functional
10 ingredient is generated by the conversion agent from at least one constituent of the food

material.

3. A foodstuff prepared from a food material, wherein the foodstuff comprises at least
one functional ingredient, and wherein the at least one functional ingredient has been

15 generated from at least one constituent of the food material by a conversion agent.

4. Invention according to claim 1 , 2 or 3 wherein the conversion agent is present in the
foodstuff .

20 5. Invention according to any one of the preceding claims wherein the conversion agent
is a catalyst.

6. Invention according to claim 5 wherein the conversion agent is an enzyme.

25 7. Invention according to claim 6 wherein the enzyme is selected from lipase, esterase,
derivatives and mixtures thereof.

8. Invention according to claim 6 or 7 wherein the enzyme is isolated from a plant, an
animal or a microorganism.

30

9. Invention according to claim 8 wherein the microorganism is selected from
Aspergillus niger, Rhizopus delemar, Rhlzopiis arrhiziis, Miicor miehei, Pseudomonas

23

sp., Candida rugosa, Pencilium roqueforti, Pencditim cyclopium, Aspergillus
tubingensis, Candida cylindracea, Thermomyces lamiginosus, Mucor javanicus,
Candida antarctica, Chromobacteriwn viscosum, Pseudomanas fluorescens, mutants
and combinations thereof.

5

10. Invention according to any one of the preceding claims wherein the conversion
agent is present in an inactive form or a denatured form in the foodstuff.

1 1 . Invention according to any one of the preceding claims wherein the functional
10 ingredient is generated from at least two constituents of the food material.

12. Invention according to any one of the preceding claims wherein the functional
ingredient is generated from a first constituent and a second constituent of the food
material.

15

13. Invention according to claim 12 wherein the first constituent and the second
constituent are constituents of the foodstuff

" 14. Invention according to claim 12 or 13 wherein the first constituent is hydrophobic
20 and/or lipophilic.

15. Invention according to any one of claims 12 to 14 wherein the first constituent is
selected from fats, oils, fatty acids, derivatives and mixtures thereof

25 16. Invention according to any one of claims 12 to 15 wherein the second constituent is
hydrophilic.

17. Invention according to any one of claims 12 to 16 wherein the second constituent is
selected from a constituent comprising a hydroxy group (-OH), polyvalent alcohols,
30 including glycerol; water, ethanol, sugars including sucrose, fructose, glucose
(dextrose), lactose, and galactose; dextnn, sorbitol, mannitoL fruit acids and hydroxy
acids including citnc acid, tartaric acid, lactic acid and ascorbic acid; mixtures and

24

derivatives thereof. More preferably, the second constituent of the food
material/foodstuff is glycerol.

18. Invention according to any one of the preceding claims wherein the foodstuff is
5 selected from baked goods, including breads, cakes, muffins, doughnuts, biscuits,

crackers and cookies; confectionery, including candies, caramels, chocolate and
puddings; frozen products, preferably frozen dairy products, including ice cream and ice
milk; dairy products, including coffee cream, whipped cream, custard cream, milk
drinks; meat products, including processed meat products; edible oils and fats, including
10 w/o emulsions, o/w emulsions, margarine shortening and spreads; fine foods, including
sauces and mayoniiaise.

19. Invention according to claim I wherein the foodstuff comprises at least two
functional ingredients, and wherein the at least two functional ingredient have been

15 generated from a first constituent of the food material and a second constituent of the
food material by a conversion agent.

20. Invention according to claim 19 wherein the first constituent is a constituent
comprising at least two ester groups, preferably a triester, more preferably a triglyceride.

20

21. Invention according to claim 19 or 20 wherein the second constituent is a sugar or 'a
sugar alcohol, more preferably ascorbic acid.

22. Use according to claim 1 substantially as hereinbefore described.

25

23. Process according to claim 2 substantially as hereinbefore described.

24. Foodstuff according to claim 3 substantially as hereinbefore described.

25

ABSTRACT
Foodstuff

There is provided use of a conversion agent to prepare from a food material a foodstuff
comprising at least one functional ingredient, wherein the at least one functional
ingredient has been generated from at least one constituent of the food material by the
conversion agent.